Epiberberine

Base Information

• Chemical Name: Epiberberine
• CAS No.: 6873-09-2
• Molecular Formula: C₂₀H₁₈NO₄
• Molecular Weight: 336.367
• UNII: VWP9N35AYS
• DSSTox Substance ID: DTXSID90218854
• Nikkaji Number: J468.363C
• Wikidata: Q72470798
• Pharos Ligand ID: 6XNHSRMYU9N7
• Metabolomics Workbench ID: 122703
• ChEMBL ID: CHEMBL1197637
• Mol file: 6873-09-2.mol

Synonyms:epiberberine

Chemical Property of Epiberberine

Chemical Property:

• Melting Point: 260oC
• PSA: 40.80000
• LogP: 3.09630
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 336.12358306
• Heavy Atom Count: 25
• Complexity: 488

Purity/Quality:

95%-98% ^*data from raw suppliers

Epiberberine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)CC[N+]3=C2C=C4C=CC5=C(C4=C3)OCO5)OC
• Uses: Epiberberine Chloride, is a natural bioactive alkaloid, an isomer of Berberine (B318150), an isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells.

Technology Process of Epiberberine

There total 13 articles about Epiberberine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

C20H19NO5 → Epiberberine (6873-09-2)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 6h;

Reference yield:

dihydroepiberberine (51665-54-4) → Epiberberine (6873-09-2)

Guidance literature:

With iodine; potassium acetate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201601245

Reference yield:

8-oxo-epiberberine (19716-60-0) → Epiberberine (6873-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere

2: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere

With aluminum (III) chloride; lithium aluminium tetrahydride; iodine; potassium acetate; In diethyl ether; ethanol;

DOI:10.1002/chem.201601245

upstream raw materials:

8-oxo-epiberberine

dihydroepiberberine

6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

5-bromo-benzo[1,3]dioxole-4-carbaldehyde

Refernces

• 1、 Zhou, Shiqiang,Tong, Rongbiao. "A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps". . p. 7084 - 7089. Retrieved 2016/05/19.